Acetic Acid → HCID 86687519, compound

HRID 1473470Notes

Reaction equation

HRID 1473470 reaction equation
FC(F)(F)C(O)=O.[NH:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[C:22]2[C:17](=[CH:18][C:19]([S:23]([O:26][C:27]3[C:32]([F:33])=[C:31]([F:34])[C:30]([F:35])=[C:29]([F:36])[C:28]=3[F:37])(=[O:25])=[O:24])=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1.[O:38]1[CH2:43][CH2:42][C:41](=O)[CH2:40][CH2:39]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl.C(OCC)(=O)C.O>[O:38]1[CH2:43][CH2:42][CH:41]([N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[C:13]2[C:22]3[C:17](=[CH:18][C:19]([S:23]([O:26][C:27]4[C:28]([F:37])=[C:29]([F:36])[C:30]([F:35])=[C:31]([F:34])[C:32]=4[F:33])(=[O:24])=[O:25])=[CH:20][CH:21]=3)[CH:16]=[CH:15][N:14]=2)[CH2:40][CH2:39]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 86687442HCID 86687442, compound

Product 1

HCID 86687519HCID 86687519, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Perfluorophenyl 1-(pyrrolidin-2-yl)isoquinoline-6-sulfonate 2,2,2-trifluoroacetate (Intermediate ZZZ; 0.100 g, 0.179 mmol) and tetrahydro-4h-pyran-4-one (0.025 ml, 0.269 mmol) were dissolved in DCM (1.791 ml). Sodium triacetoxyborohydride (0.114 g, 0.537 mmol) and acetic acid (0.015 ml, 0.269 mmol) were added and the reaction was stirred for one hour at room temperature. Water was added followed by ethyl acetate. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with brine, dried with sodium sulfate, filtered, and concentrated to afford perfluorophenyl 1-(1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-2-yl)isoquinoline-6-sulfonate as an oily blue solid. m/z (ESI) 529.3 (M+H)+.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7f79ba6e4c764814a1f1297c51cfbee0
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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